176167-06-9

Upstream product

• 157363-87-6 N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 172147-87-4 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,5-diol 
• 172147-86-3 Methanesulfonic acid (1R,2S,3S,4R)-2,3-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methanesulfonyloxy-pentyl ester 
• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 

Relevant academic research and scientific papers

Synthesis of azasugars as potent inhibitors of glycosidases

A series of enantiomerically pure azasugars (2,5-dideoxy-2,5-imino-D-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from D-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-D-glucosidases, α-D-mannosidase and α-L-fucosidase). Inhibition studies indicate notably that the polyhydroxylated azepanes are inhibitors of glycosidases, with K(i) in the micromolar range.

Synthesis of azasugars. Part 2: Isomerization of polyhydroxylated azepanes

Isomerization of enantiopure C2-symmetric 3,5-dihydroxyazepane derivatives has been studied. The neighboring nitrogen participation occurs during mesylation to give a chloromethyl-piperidine, whereas from the L-ido-azepane a chiral bridged morp